Dimethylamine → Drometrizole

HRID 2082169Notes

Reaction equation

HRID 2082169 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[OH:19])([O-])=O.C1(C)C=CC=CC=1.CNC.[H][H]>[C].[Pd].O.CC(O)C>[OH:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[N:11]1[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[N:1]1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 1140TolueneHCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 17113DrometrizoleYield 81%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

25.7 g (0.1 mol) of 2-nitro-2'-hydroxy-5'-methylazobenzene, 0.125 g of palladium carbon, 100 ml of toluene, 50 ml of IPA, 25 ml of water and 7 g of 50% dimethylamine were charged into a 500-ml stainless autoclave with an agitator. After the air in the flask had been replaced by hydrogen, the pressure of hydrogen was set to 10 kg/cm2. Reaction was then effected in the same way as that employed in Example 1. After the reaction had been completed, the catalyst was filtered off, and part of the filtrate was subjected to quantitative analysis using gas chromatography (GC). The results revealed a yield of 81% of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole. The toluene layer was separated, and most part of toluene was then distilled off from the layer. The residual solid was then crystallized using ethanol and then dried to obtain 15.7 g of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole (yield, 69.8%; melting point, 128° to 130° C.).

Workup

  1. customReaction
  2. filtrationthe catalyst was filtered off

Sources & evidence

ORD record
ord-c758086a63ac41cb91608495497ceca9
Source dataset
uspto-grants-1993_02
Patent number
US05187289

Reaction notes

Loading…